(1S)-1-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-((2S)-oxiran-2-yl)-ethyl tert-butyldimethyl-silyl ether | 1291066-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-((2S)-oxiran-2-yl)-ethyl tert-butyldimethyl-silyl ether
• 英文别名: tert-butyl-[(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(2S)-oxiran-2-yl]ethoxy]-dimethylsilane
• CAS: 1291066-68-6
• 化学式: C₁₅H₃₀O₄Si
• 分子量: 302.486
• InChiKey: SDTAPLNDACVPCZ-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-1-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-((2S)-oxiran-2-yl)-ethyl tert-butyldimethyl-silyl ether 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 silica-supported sodium periodate 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 (3S,5S,6S)-3-triisopropylsilyloxy-5-tert-butyldimethylsilyloxy-6-ethoxycarbonyloxy-hept-1-ene
  参考文献：
  名称：

  Synthesis of hept-6-en-2,4,5-triols and hept-6-en-2,3,5-triols

  摘要：

  In a systematic effort to establish the relative as well as absolute configurations of two natural products isolated from Asomycete Daldinia concentrica, four independent (non-antipodal) diastereomers of hept-6-en-2,4,5-triol, the structure previously proposed for the natural products, were synthesized in enantiopure forms through a chiral-pool route and their optical rotation as well as NMR data were recorded. Although these four synthetic isomers cover all possible relative configurations the originally assigned triol may have, none of them gave spectroscopic data compatible with those reported for the natural products. Similar negative results were also obtained with a group of four non-antipodal diastereomers of hept-6-en-2,3,5-triol. The genuine structures of the natural products are therefore to be re-assigned. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.091
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 (2R,3S,5S)-5,6-Epoxy-1,2-O-isopropylidenehexane-1,2,3-triol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以92%的产率得到(1S)-1-((4R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-((2S)-oxiran-2-yl)-ethyl tert-butyldimethyl-silyl ether
  参考文献：
  名称：

  Synthesis of hept-6-en-2,4,5-triols and hept-6-en-2,3,5-triols

  摘要：

  In a systematic effort to establish the relative as well as absolute configurations of two natural products isolated from Asomycete Daldinia concentrica, four independent (non-antipodal) diastereomers of hept-6-en-2,4,5-triol, the structure previously proposed for the natural products, were synthesized in enantiopure forms through a chiral-pool route and their optical rotation as well as NMR data were recorded. Although these four synthetic isomers cover all possible relative configurations the originally assigned triol may have, none of them gave spectroscopic data compatible with those reported for the natural products. Similar negative results were also obtained with a group of four non-antipodal diastereomers of hept-6-en-2,3,5-triol. The genuine structures of the natural products are therefore to be re-assigned. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.091

文献信息

• Synthesis and configuration of the nonadecenetriol isolated from seeds of Persea americana
  作者：Xin Yan、Shao-Min Zhang、Yikang Wu、Po Gao

  DOI：10.1039/c1ob05898c

  日期：——

  In an effort to establish the relative as well as absolute configuration of the trypanocidally active natural nonadec-6-en-1,2,4-triol isolated from Persea americana, the (2S,4R), (2S,4S), and (2R,4R) isomers were synthesized. The stereogenic centers taken from enantiopure chiral epoxy building blocks derived from inexpensive and readily available D-glucolactone. The (2R,4R) isomer gave 1H and 13C NMR as well as specific rotation in excellent consistence with those reported for the natural triol.

  为了确定从鳄梨中分离出的具有杀锥虫活性的天然十九碳-6-烯-1,2,4-三醇的相对和绝对构型，合成了(2S,4R)、(2S,4S)和(2R,4R)三种异构体。这些手性中心来自于由廉价且易得的D-古洛内酯衍生的对映纯手性环氧构建模块。其中，(2R,4R)异构体在氢谱和碳谱核磁共振以及比旋光度方面与报道的天然三醇数据高度一致。
• Synthesis and configurations of YF-0200R A and B
  作者：Xiao-Dan Wang、Ze-Jun Xu、Shijun Zhu、Yikang Wu、Yan-Jun Hou

  DOI：10.1016/j.tet.2016.04.033

  日期：2016.6

  samples were in excellent consistency with those reported for the corresponding natural ones. The optical rotations were also compatible with those for the natural ones. The absolute configurations for natural YF-0200R A and B thus could be reliably assigned as (8S) and (8S,10S), respectively.

  首次合成了两种具有天冬酰胺蛋白酶抑制活性的天然不饱和脂肪酸。通过分别使用布朗不对称烯丙基化或衍生自d-葡萄糖的手性结构单元来安装立体异构中心。经由HWE反应引入共轭二烯单元。通过C 6 D 6中的1 H NMR，C C双键的几何结构清楚地显示为（E）。。合成样品的光谱数据与相应天然样品的光谱数据具有极好的一致性。旋光度也与自然旋光度兼容。因此，可以将自然YF-0200RA和B的绝对配置分别可靠地指定为（8 S）和（8 S，10 S）。
• Synthesis of hept-6-en-2,4,5-triols and hept-6-en-2,3,5-triols
  作者：Ping Jiang、Shao-Min Zhang、Lei He、Yikang Wu、Yan Li

  DOI：10.1016/j.tet.2011.01.091

  日期：2011.4

  In a systematic effort to establish the relative as well as absolute configurations of two natural products isolated from Asomycete Daldinia concentrica, four independent (non-antipodal) diastereomers of hept-6-en-2,4,5-triol, the structure previously proposed for the natural products, were synthesized in enantiopure forms through a chiral-pool route and their optical rotation as well as NMR data were recorded. Although these four synthetic isomers cover all possible relative configurations the originally assigned triol may have, none of them gave spectroscopic data compatible with those reported for the natural products. Similar negative results were also obtained with a group of four non-antipodal diastereomers of hept-6-en-2,3,5-triol. The genuine structures of the natural products are therefore to be re-assigned. (C) 2011 Elsevier Ltd. All rights reserved.